Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E,E)-3,3'-(4-Hydroxy-1,3-phenylene)bis-2-propenoic Acid Dimethyl Ester

HRID 328008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 328008
[CH:1]([C:3]1[CH:10]=[C:7]([CH:8]=O)[C:6]([OH:11])=[CH:5][CH:4]=1)=O.C1(P(=[CH:31][C:32]([O:34][CH3:35])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:35][O:34][C:32](=[O:33])/[CH:31]=[CH:1]/[C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7](/[CH:8]=[CH:31]/[C:32]([O:34][CH3:35])=[O:33])[CH:10]=1

Komponenten

4

Edukt 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 1651064-Hydroxyisophthalaldehyde

Produkt 1

HCID 10706586(E,E)-3,3'-(4-Hydroxy-1,3-phenylene)bis-2-propenoic Acid Dimethyl EsterAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g (33.3 mmol) of 5-formylsalicylaldehyde and 24.5 g (73.3 mmol) of methyl (triphenyl phosphoranylidene)acetate, in 150 mL of toluene was stirred and refluxed for 2.5 hr and then kept at room temperature overnight. The solvent was removed in vacuo and the solid residue was flash-chromatographed on silica gel. There was obtained 8.07 g (92.5%) of the title compound as a colorless solid.

Aufarbeitung

  1. temperaturerefluxed for 2.5 hr
  2. customThe solvent was removed in vacuo
  3. customthe solid residue was flash-chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-271eb7ad8070462a9b6ed5dd886a484b
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273999

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